Director of Finance - Controller

Who We Are

Chesapeake Employers’ Insurance Company is a purpose-driven organization dedicated to improving the lives and livelihoods of our policyholders, injured workers, team members, and the community. As a leading workers' compensation specialty insurer in the mid-Atlantic region, we take pride in being a force for good. Our 350 team members are committed to making a positive impact every day in the lives of all our stakeholders.

Join our motivated, professional team as we foster a culture of values, teamwork, innovation, and collaboration. Established in 1914, Chesapeake Employers Insurance, headquartered in Towson, Maryland, has over a century of experience, a strong financial foundation, and an "A" rating from AM Best.

Manages the financial reporting function within Finance to provide accurate information for reporting and to support management in decision-making, as well as timely services to internal customers. Oversees accounting operations, financial close process, financial statement presentation and reporting, audit coordination, accounts payable, payroll, fixed assets, and other key responsibilities as needed. Ensures resource development and allocation to deliver services efficiently and productively.

• Contributes to the achievement of established department goals and objectives; adheres to departmental policies, procedures, quality and safety standards, and consistently exhibits Chesapeake’s Values and Behaviors.
• Provides performance feedback to direct reports; conducts regular performance evaluations and provides constructive feedback and coaching to enhance individual and team effectiveness.
• Actively participates and makes recommendations for personnel actions including hiring, promoting, and disciplinary measures in alignment with organizational and department policies.
• Guides and supports the training and professional development of direct reports, fostering a culture of continuous improvement and technical experience.
• Participates in cross-functional projects and initiatives supporting key organizational and operational outcomes.
• Partners with leadership on decision support.
• Leads the month-end closing and financial reporting processes.
• Responsible for internal controls and financial policies over financial reporting.
• Supports Board and Executive reporting, including the preparation of quarterly financial board packages and monthly key performance indicators.
• Oversees the preparation of quarterly and annual filings for the NAIC and Maryland Insurance Administration.
• Supervises accounting staff, accounts payable, payroll, and other Finance functions as assigned.
• Develops system controls and reconciliations to ensure data integrity.
• Identifies areas for improvement and leads continuous process improvements within functions.
• Oversees the administration of various accounting systems, including but not limited to the general ledger, accounts payable, fixed assets, and payroll systems.
• Interfaces regularly with internal and external auditors and regulators regarding internal controls and financial reporting.
• Acts as primary liaison for various external audits.
• Other duties and project work as assigned.

• Thorough knowledge of GAAP and exposure to statutory accounting.
• Strong communication and interpersonal skills.
• Strong organizational and time management skills.
• Leadership and supervisory skills.

• Bachelor s degree in Accounting or CPA required.
• Ten (10) years of accounting experience.
• Five (5) years of supervisory experience.
• Advanced Excel skills.
• Effectively utilizes technologies and tools, including Microsoft 365 and role-specific platforms, to support productivity and efficient work practices.

• CPA or Master s Degree in Business or Finance.
• Insurance accounting experience.

This job description is intended to describe the general nature and level of work being performed. It is not an exhaustive list of all responsibilities, duties, and skills required. Reasonable accommodation may be made to enable individuals with disabilities to perform the essential functions.

While…